Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCOC(C)CNC(=O)OC(C)(C)C
InChiKey
BSRLSVISCTTZEI-UHFFFAOYSA-N
Route Signature
8d8be53da771edf8b0d19c41bbeaa073d4ebba7ed89eebc1dd6fbd0ce02d8799
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1460748410d7c7c8a076ea5a",
"signature": "8d8be53da771edf8b0d19c41bbeaa073d4ebba7ed89eebc1dd6fbd0ce02d8799",
"contentHash": "c6c0696c148df1227109acfd73281341041f9bfa5dd9b6dfc6ff8946228fb979",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_f8aab8ba4e4365cf75171a2d",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00386",
"moleculeId": "sa_ce0755d69b1518cf9339254d",
"smiles": "COCCOC(C)CNC(=O)OC(C)(C)C",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_ce0755d69b1518cf9339254d",
"inchikey": "BSRLSVISCTTZEI-UHFFFAOYSA-N",
"smiles": "COCCOC(C)CNC(=O)OC(C)(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4189",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_ce0755d69b1518cf9339254d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ce0755d69b1518cf9339254d",
"inchikey": "BSRLSVISCTTZEI-UHFFFAOYSA-N",
"smiles": "COCCOC(C)CNC(=O)OC(C)(C)C"
},
"smiles": "COCCOC(C)CNC(=O)OC(C)(C)C",
"reactionStepId": "sa_2dadbf1f595c343433f949d9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100234351A1;1380;942856\",\"rsmi\":\"I[CH3:1].[OH:2][CH2:3][CH2:4][O:5][CH:6]([CH3:7])[CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]>C1CCOC1.[HH].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH:6]([CH3:7])[CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][CH2:3][CH2:4][O:5][CH:6]([CH3:7])[CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]>C1CCOC1.[HH].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH:6]([CH3:7])[CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]\"}",
"reactionStep": {
"id": "sa_2dadbf1f595c343433f949d9",
"reactionHash": "2e4ffe1bbe9f41c38c0f4af7ace9d8dc9fad53329292e5bc1a3ba691ab941e86"
},
"children": [
{
"id": "4190",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_7fd8a9d556615461d8682074",
"parentId": "4189",
"isLeaf": false,
"molecule": {
"id": "sa_7fd8a9d556615461d8682074",
"inchikey": "FBXOBMLSKOHXQR-UHFFFAOYSA-N",
"smiles": "CC(CNC(=O)OC(C)(C)C)OCCO"
},
"smiles": "CC(CNC(=O)OC(C)(C)C)OCCO",
"reactionStepId": "sa_d70596655892f23d71d79e11",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100234351A1;1373;942853\",\"rsmi\":\"c1ccc(C[O:15][CH2:14][CH2:13][O:12][CH:2]([CH3:1])[CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])cc1>C.CO.[Pd]>[CH3:1][CH:2]([CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[O:12][CH2:13][CH2:14][OH:15]\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:15][CH2:14][CH2:13][O:12][CH:2]([CH3:1])[CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])cc1>C.CO.[Pd]>[CH3:1][CH:2]([CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[O:12][CH2:13][CH2:14][OH:15]\"}",
"reactionStep": {
"id": "sa_d70596655892f23d71d79e11",
"reactionHash": "0a5341940353ebc0ebb6a8208097e86edca7c657b5cc11b1070537ac45cab2ed"
},
"children": [
{
"id": "4191",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_e2c61df77d714c7f6ae998a7",
"parentId": "4190",
"isLeaf": false,
"molecule": {
"id": "sa_e2c61df77d714c7f6ae998a7",
"inchikey": "NAJRXCQVPQRKRR-UHFFFAOYSA-N",
"smiles": "CC(CNC(=O)OC(C)(C)C)OCCOCc1ccccc1"
},
"smiles": "CC(CNC(=O)OC(C)(C)C)OCCOCc1ccccc1",
"reactionStepId": "sa_918f8152748811bddeb376f0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100234351A1;1371;942852\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11].[N-]=[N+]=[N:4][CH2:3][CH:2]([CH3:1])[O:12][CH2:13][CH2:14][O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>C1CCOC1.CCN(CC)CC.CO.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[O:12][CH2:13][CH2:14][O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11].[N-]=[N+]=[N:4][CH2:3][CH:2]([CH3:1])[O:12][CH2:13][CH2:14][O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>C1CCOC1.CCN(CC)CC.CO.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[O:12][CH2:13][CH2:14][O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_918f8152748811bddeb376f0",
"reactionHash": "777fa6400a682e71d8a3f64911f87e0dea78e7241d72af928fbcd78f1657e1fb"
},
"children": [
{
"id": "4192",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "4191",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4193",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_08148035f988d36701fc310c",
"parentId": "4191",
"isLeaf": false,
"molecule": {
"id": "sa_08148035f988d36701fc310c",
"inchikey": "JXMGICFBSZEMNL-UHFFFAOYSA-N",
"smiles": "CC(CN=[N+]=[N-])OCCOCc1ccccc1"
},
"smiles": "CC(CN=[N+]=[N-])OCCOCc1ccccc1",
"reactionStepId": "sa_9c16a315b79f873a1fc6a91d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100234351A1;1369;942851\",\"rsmi\":\"O[CH2:3][CH:2]([CH3:1])[O:7][CH2:8][CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[N-:4]=[N+:5]=[N-:6]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.CS(=O)(=O)Cl.[Na+]>[CH3:1][CH:2]([CH2:3][N:4]=[N+:5]=[N-:6])[O:7][CH2:8][CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O[CH2:3][CH:2]([CH3:1])[O:7][CH2:8][CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[N-:4]=[N+:5]=[N-:6]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.CS(=O)(=O)Cl.[Na+]>[CH3:1][CH:2]([CH2:3][N:4]=[N+:5]=[N-:6])[O:7][CH2:8][CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_9c16a315b79f873a1fc6a91d",
"reactionHash": "b8a90973a30efc5e52f3e0479419fce0d04229420199e5f36122ca167c9b88fb"
},
"children": [
{
"id": "4194",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "4193",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4195",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_3968a25defbf9075785de0a1",
"parentId": "4193",
"isLeaf": false,
"molecule": {
"id": "sa_3968a25defbf9075785de0a1",
"inchikey": "NITCSOASVFRRFB-UHFFFAOYSA-N",
"smiles": "CC(CO)OCCOCc1ccccc1"
},
"smiles": "CC(CO)OCCOCc1ccccc1",
"reactionStepId": "sa_10a875a2b51e3c5b5db5cabc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100234351A1;1367;942850\",\"rsmi\":\"COc1ccc([O:4][CH2:3][CH:2]([CH3:1])[O:5][CH2:6][CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)cc1>CC#N.O.O=C(O)O.O=S(O)O.O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])O.[Ce+3].N.N.[Na+].[Na+].[Na+]>[CH3:1][CH:2]([CH2:3][OH:4])[O:5][CH2:6][CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"COc1ccc([O:4][CH2:3][CH:2]([CH3:1])[O:5][CH2:6][CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)cc1>CC#N.O.O=C(O)O.O=S(O)O.O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])O.[Ce+3].N.N.[Na+].[Na+].[Na+]>[CH3:1][CH:2]([CH2:3][OH:4])[O:5][CH2:6][CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "e09850e7348ca81e3a77dd220c82b49add031d26e3f2b02080f1919299be80af"
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"children": [
{
"id": "4196",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_c6e79319bbb5caf43be8ba9d",
"parentId": "4195",
"isLeaf": false,
"molecule": {
"id": "sa_c6e79319bbb5caf43be8ba9d",
"inchikey": "JRVXUVZUSIECKR-UHFFFAOYSA-N",
"smiles": "COc1ccc(OCC(C)OCCOCc2ccccc2)cc1"
},
"smiles": "COc1ccc(OCC(C)OCCOCc2ccccc2)cc1",
"reactionStepId": "sa_8645595302f10e5c35ed70f0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100234351A1;1365;942849\",\"rsmi\":\"Br[CH2:12][CH2:13][O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([CH3:10])[OH:11])[cH:22][cH:23]1>CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccccc1.O=S(=O)(O)O.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([CH3:10])[O:11][CH2:12][CH2:13][O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"Br[CH2:12][CH2:13][O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([CH3:10])[OH:11])[cH:22][cH:23]1>CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccccc1.O=S(=O)(O)O.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([CH3:10])[O:11][CH2:12][CH2:13][O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_8645595302f10e5c35ed70f0",
"reactionHash": "737132719a02c9071ca739dbfb4328b23c13ad8b6059db4a2f0b3f6d417dc4a3"
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"children": [
{
"id": "4197",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_0c1a55fe5cb9abe2ceb117d3",
"parentId": "4196",
"isLeaf": true,
"molecule": {
"id": "sa_0c1a55fe5cb9abe2ceb117d3",
"inchikey": "FWOHDAGPWDEWIB-UHFFFAOYSA-N",
"smiles": "BrCCOCc1ccccc1"
},
"smiles": "BrCCOCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4198",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_b3cd4c80ec1cd479d676fa35",
"parentId": "4196",
"isLeaf": true,
"molecule": {
"id": "sa_b3cd4c80ec1cd479d676fa35",
"inchikey": "VRJJZESAMSRBTH-UHFFFAOYSA-N",
"smiles": "COc1ccc(OCC(C)O)cc1"
},
"smiles": "COc1ccc(OCC(C)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
},
{
"id": "4199",
"routeId": "sa_1460748410d7c7c8a076ea5a",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "4189",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}